data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'John C. Walton' 'Eoin M. Scanlan' 'Alexandra M.Z. Slawin' _publ_contact_author_name 'Prof John C. Walton' _publ_contact_author_address ; Chemistry University of St. Andrews North Haugh St. Andrews UNITED KINGDOM ; _publ_contact_author_email JCW@ST-AND.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Preparation of beta- and gamma-lactams from carbamoyl radicals derived from oxime oxalate amides ; data_7B _database_code_depnum_ccdc_archive 'CCDC 225168' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H24 N2 O5 S' _chemical_formula_sum 'C20 H24 N2 O5 S' _chemical_formula_weight 404.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.9072(13) _cell_length_b 18.141(3) _cell_length_c 12.9956(19) _cell_angle_alpha 90.00 _cell_angle_beta 94.949(3) _cell_angle_gamma 90.00 _cell_volume 2092.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 128 _cell_measurement_theta_min 12 _cell_measurement_theta_max 168 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .1 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.187 _exptl_absorpt_correction_type MULTISCAN _exptl_absorpt_correction_T_min 0.708574 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0.9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8782 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 23.27 _reflns_number_total 2956 _reflns_number_gt 2569 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0517P)^2^+0.4950P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment RIDING _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0042(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2956 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0868 _refine_ls_wR_factor_gt 0.0831 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.32030(15) 0.36145(7) 0.50242(11) 0.0214(3) Uani 1 1 d . . . C2 C 0.47675(18) 0.35655(9) 0.47082(13) 0.0218(4) Uani 1 1 d . . . H2A H 0.5123 0.4063 0.4502 0.026 Uiso 1 1 calc R . . S3 S 0.45836(5) 0.29538(2) 0.35946(3) 0.02627(16) Uani 1 1 d . . . C4 C 0.2637(2) 0.32473(10) 0.32353(14) 0.0257(4) Uani 1 1 d . . . C5 C 0.19819(18) 0.33474(9) 0.42951(13) 0.0224(4) Uani 1 1 d . . . H5A H 0.1167 0.3728 0.4224 0.027 Uiso 1 1 calc R . . C6 C 0.28346(18) 0.38909(9) 0.59284(13) 0.0210(4) Uani 1 1 d . . . O6 O 0.15458(13) 0.39016(7) 0.61902(9) 0.0292(3) Uani 1 1 d . . . C7 C 0.40885(18) 0.42637(9) 0.66227(13) 0.0209(4) Uani 1 1 d . . . O7 O 0.47141(13) 0.48114(6) 0.63769(9) 0.0262(3) Uani 1 1 d . . . O8 O 0.42306(13) 0.39258(6) 0.75455(9) 0.0248(3) Uani 1 1 d . . . N9 N 0.53859(16) 0.42638(8) 0.82511(11) 0.0254(3) Uani 1 1 d . . . C10 C 0.52072(19) 0.40260(9) 0.91530(13) 0.0230(4) Uani 1 1 d . . . H10A H 0.4409 0.3694 0.9257 0.028 Uiso 1 1 calc R . . C11 C 0.62398(18) 0.42653(9) 1.00351(13) 0.0221(4) Uani 1 1 d . . . C12 C 0.6073(2) 0.39643(10) 1.10033(14) 0.0274(4) Uani 1 1 d . . . H12A H 0.5315 0.3605 1.1079 0.033 Uiso 1 1 calc R . . C13 C 0.7007(2) 0.41863(11) 1.18616(15) 0.0330(5) Uani 1 1 d . . . H13A H 0.6890 0.3977 1.2520 0.040 Uiso 1 1 calc R . . C14 C 0.8105(2) 0.47106(12) 1.17526(15) 0.0355(5) Uani 1 1 d . . . H14A H 0.8740 0.4866 1.2337 0.043 Uiso 1 1 calc R . . C15 C 0.8280(2) 0.50101(11) 1.07899(15) 0.0350(5) Uani 1 1 d . . . H15A H 0.9040 0.5369 1.0717 0.042 Uiso 1 1 calc R . . C16 C 0.7360(2) 0.47913(10) 0.99337(14) 0.0288(4) Uani 1 1 d . . . H16A H 0.7490 0.4999 0.9276 0.035 Uiso 1 1 calc R . . C17 C 0.58350(19) 0.32492(9) 0.55478(14) 0.0250(4) Uani 1 1 d . . . H17A H 0.5546 0.2803 0.5859 0.030 Uiso 1 1 calc R . . C18 C 0.71548(19) 0.35403(10) 0.58949(14) 0.0273(4) Uani 1 1 d . . . C19 C 0.8098(2) 0.31889(13) 0.67753(17) 0.0432(5) Uani 1 1 d . . . H19A H 0.8134 0.3513 0.7380 0.065 Uiso 1 1 calc R . . H19B H 0.9121 0.3109 0.6576 0.065 Uiso 1 1 calc R . . H19C H 0.7653 0.2715 0.6945 0.065 Uiso 1 1 calc R . . C20 C 0.7813(2) 0.42303(11) 0.54789(17) 0.0380(5) Uani 1 1 d . . . H20A H 0.7102 0.4441 0.4940 0.057 Uiso 1 1 calc R . . H20B H 0.8761 0.4112 0.5185 0.057 Uiso 1 1 calc R . . H20C H 0.8006 0.4588 0.6039 0.057 Uiso 1 1 calc R . . C21 C 0.2591(2) 0.39792(10) 0.26504(15) 0.0304(4) Uani 1 1 d . . . H21A H 0.3054 0.3916 0.1999 0.046 Uiso 1 1 calc R . . H21B H 0.3148 0.4354 0.3072 0.046 Uiso 1 1 calc R . . H21C H 0.1542 0.4137 0.2506 0.046 Uiso 1 1 calc R . . C22 C 0.1834(2) 0.26501(11) 0.25736(14) 0.0334(5) Uani 1 1 d . . . H22A H 0.0768 0.2781 0.2433 0.050 Uiso 1 1 calc R . . H22B H 0.1917 0.2178 0.2942 0.050 Uiso 1 1 calc R . . H22C H 0.2299 0.2607 0.1920 0.050 Uiso 1 1 calc R . . C23 C 0.1329(2) 0.26316(10) 0.46732(13) 0.0262(4) Uani 1 1 d . . . O23 O 0.20454(15) 0.21345(7) 0.50850(10) 0.0336(3) Uani 1 1 d . . . O24 O -0.01648(14) 0.26260(7) 0.44390(10) 0.0326(3) Uani 1 1 d . . . C25 C -0.0936(2) 0.19566(11) 0.46838(17) 0.0439(5) Uani 1 1 d . . . H25A H -0.0588 0.1550 0.4269 0.066 Uiso 1 1 calc R . . H25B H -0.2024 0.2022 0.4529 0.066 Uiso 1 1 calc R . . H25C H -0.0719 0.1844 0.5419 0.066 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0206(7) 0.0212(7) 0.0223(8) -0.0029(6) 0.0007(6) -0.0016(6) C2 0.0209(9) 0.0196(9) 0.0252(10) -0.0011(7) 0.0028(7) -0.0009(7) S3 0.0298(3) 0.0248(3) 0.0246(3) -0.00352(18) 0.00471(19) 0.00061(18) C4 0.0291(10) 0.0255(9) 0.0221(9) -0.0018(7) 0.0007(7) -0.0058(8) C5 0.0212(9) 0.0214(9) 0.0238(9) -0.0035(7) -0.0028(7) -0.0031(7) C6 0.0225(10) 0.0166(8) 0.0238(9) 0.0021(7) 0.0008(7) -0.0008(7) O6 0.0248(7) 0.0368(7) 0.0264(7) -0.0026(5) 0.0037(5) -0.0024(6) C7 0.0224(9) 0.0190(9) 0.0212(9) -0.0022(7) 0.0017(7) 0.0027(8) O7 0.0307(7) 0.0209(6) 0.0262(7) 0.0001(5) -0.0015(5) -0.0031(5) O8 0.0296(6) 0.0257(6) 0.0182(6) -0.0001(5) -0.0022(5) -0.0056(5) N9 0.0255(8) 0.0280(8) 0.0214(9) -0.0024(6) -0.0044(6) -0.0022(6) C10 0.0269(9) 0.0187(8) 0.0235(10) -0.0025(7) 0.0030(7) 0.0037(7) C11 0.0253(9) 0.0202(9) 0.0209(9) -0.0044(7) 0.0016(7) 0.0078(7) C12 0.0340(10) 0.0237(9) 0.0248(10) -0.0021(7) 0.0049(8) 0.0039(8) C13 0.0414(11) 0.0367(11) 0.0208(10) -0.0030(8) 0.0019(8) 0.0116(9) C14 0.0320(11) 0.0472(12) 0.0258(11) -0.0120(9) -0.0059(8) 0.0087(9) C15 0.0299(10) 0.0402(11) 0.0346(11) -0.0076(9) 0.0002(8) -0.0038(9) C16 0.0307(10) 0.0301(10) 0.0256(10) 0.0005(8) 0.0024(8) 0.0014(8) C17 0.0271(10) 0.0211(9) 0.0268(10) 0.0015(7) 0.0030(7) 0.0046(7) C18 0.0222(9) 0.0297(10) 0.0299(10) -0.0024(8) 0.0013(7) 0.0067(8) C19 0.0344(11) 0.0537(14) 0.0397(12) 0.0038(10) -0.0075(9) 0.0091(10) C20 0.0237(10) 0.0365(11) 0.0528(13) 0.0012(9) -0.0034(9) -0.0020(8) C21 0.0305(10) 0.0322(11) 0.0281(10) 0.0062(8) -0.0005(8) -0.0053(8) C22 0.0425(11) 0.0335(11) 0.0241(10) -0.0055(8) 0.0016(8) -0.0115(9) C23 0.0310(10) 0.0286(10) 0.0193(9) -0.0052(8) 0.0039(7) -0.0064(8) O23 0.0454(8) 0.0289(7) 0.0265(7) 0.0040(6) 0.0021(6) -0.0049(6) O24 0.0294(7) 0.0331(7) 0.0354(8) -0.0036(6) 0.0042(5) -0.0137(6) C25 0.0450(12) 0.0404(12) 0.0476(13) -0.0046(10) 0.0109(10) -0.0237(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C6 1.344(2) . ? N1 C5 1.462(2) . ? N1 C2 1.489(2) . ? C2 C17 1.498(2) . ? C2 S3 1.8197(17) . ? S3 C4 1.8350(18) . ? C4 C22 1.523(2) . ? C4 C21 1.529(3) . ? C4 C5 1.552(3) . ? C5 C23 1.521(2) . ? C6 O6 1.225(2) . ? C6 C7 1.531(2) . ? C7 O7 1.196(2) . ? C7 O8 1.343(2) . ? O8 N9 1.4536(18) . ? N9 C10 1.272(2) . ? C10 C11 1.472(2) . ? C11 C12 1.391(3) . ? C11 C16 1.395(3) . ? C12 C13 1.393(3) . ? C13 C14 1.380(3) . ? C14 C15 1.385(3) . ? C15 C16 1.382(3) . ? C17 C18 1.332(2) . ? C18 C19 1.501(3) . ? C18 C20 1.503(3) . ? C23 O23 1.203(2) . ? C23 O24 1.339(2) . ? O24 C25 1.444(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C5 117.79(14) . . ? C6 N1 C2 124.63(13) . . ? C5 N1 C2 117.58(13) . . ? N1 C2 C17 111.85(14) . . ? N1 C2 S3 103.51(10) . . ? C17 C2 S3 110.71(12) . . ? C2 S3 C4 92.51(8) . . ? C22 C4 C21 110.24(15) . . ? C22 C4 C5 112.94(15) . . ? C21 C4 C5 110.09(15) . . ? C22 C4 S3 108.96(13) . . ? C21 C4 S3 111.28(12) . . ? C5 C4 S3 103.15(11) . . ? N1 C5 C23 110.93(14) . . ? N1 C5 C4 107.34(13) . . ? C23 C5 C4 111.73(14) . . ? O6 C6 N1 123.63(15) . . ? O6 C6 C7 118.85(15) . . ? N1 C6 C7 117.34(14) . . ? O7 C7 O8 127.41(15) . . ? O7 C7 C6 122.84(15) . . ? O8 C7 C6 109.41(14) . . ? C7 O8 N9 112.20(12) . . ? C10 N9 O8 107.47(14) . . ? N9 C10 C11 119.88(16) . . ? C12 C11 C16 119.15(16) . . ? C12 C11 C10 118.69(16) . . ? C16 C11 C10 122.15(16) . . ? C11 C12 C13 120.50(18) . . ? C14 C13 C12 119.80(18) . . ? C13 C14 C15 119.93(17) . . ? C16 C15 C14 120.62(18) . . ? C15 C16 C11 119.98(17) . . ? C18 C17 C2 125.53(16) . . ? C17 C18 C19 120.61(17) . . ? C17 C18 C20 124.69(16) . . ? C19 C18 C20 114.70(16) . . ? O23 C23 O24 125.02(16) . . ? O23 C23 C5 125.49(16) . . ? O24 C23 C5 109.44(15) . . ? C23 O24 C25 116.00(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 C17 47.3(2) . . . . ? C5 N1 C2 C17 -133.14(15) . . . . ? C6 N1 C2 S3 166.52(13) . . . . ? C5 N1 C2 S3 -13.93(16) . . . . ? N1 C2 S3 C4 29.75(11) . . . . ? C17 C2 S3 C4 149.75(13) . . . . ? C2 S3 C4 C22 -157.73(13) . . . . ? C2 S3 C4 C21 80.52(13) . . . . ? C2 S3 C4 C5 -37.49(12) . . . . ? C6 N1 C5 C23 -71.71(18) . . . . ? C2 N1 C5 C23 108.71(17) . . . . ? C6 N1 C5 C4 165.97(14) . . . . ? C2 N1 C5 C4 -13.61(19) . . . . ? C22 C4 C5 N1 151.51(15) . . . . ? C21 C4 C5 N1 -84.79(16) . . . . ? S3 C4 C5 N1 34.04(15) . . . . ? C22 C4 C5 C23 29.7(2) . . . . ? C21 C4 C5 C23 153.39(14) . . . . ? S3 C4 C5 C23 -87.77(14) . . . . ? C5 N1 C6 O6 3.2(2) . . . . ? C2 N1 C6 O6 -177.21(15) . . . . ? C5 N1 C6 C7 -171.92(14) . . . . ? C2 N1 C6 C7 7.6(2) . . . . ? O6 C6 C7 O7 -111.41(19) . . . . ? N1 C6 C7 O7 64.0(2) . . . . ? O6 C6 C7 O8 62.40(19) . . . . ? N1 C6 C7 O8 -122.20(16) . . . . ? O7 C7 O8 N9 -5.4(2) . . . . ? C6 C7 O8 N9 -178.83(12) . . . . ? C7 O8 N9 C10 165.41(14) . . . . ? O8 N9 C10 C11 178.97(13) . . . . ? N9 C10 C11 C12 -176.35(16) . . . . ? N9 C10 C11 C16 4.7(2) . . . . ? C16 C11 C12 C13 0.2(3) . . . . ? C10 C11 C12 C13 -178.77(15) . . . . ? C11 C12 C13 C14 0.2(3) . . . . ? C12 C13 C14 C15 -0.5(3) . . . . ? C13 C14 C15 C16 0.3(3) . . . . ? C14 C15 C16 C11 0.2(3) . . . . ? C12 C11 C16 C15 -0.4(3) . . . . ? C10 C11 C16 C15 178.54(16) . . . . ? N1 C2 C17 C18 -130.10(18) . . . . ? S3 C2 C17 C18 115.03(17) . . . . ? C2 C17 C18 C19 177.25(17) . . . . ? C2 C17 C18 C20 -1.6(3) . . . . ? N1 C5 C23 O23 -39.9(2) . . . . ? C4 C5 C23 O23 79.8(2) . . . . ? N1 C5 C23 O24 142.62(14) . . . . ? C4 C5 C23 O24 -97.65(16) . . . . ? O23 C23 O24 C25 -1.8(3) . . . . ? C5 C23 O24 C25 175.74(15) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.297 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.044